Δ22 -derivatives of LL-F28249 compounds

Abstract

The present invention relates to novel derivatives of LL-F28249 compounds. These LL-F28249 compounds preferably are derived via a controlled microbiological fermentation of Streptomyces cyaneogriseus subsp. non-cyanogenus having deposit accession numer NRRL 15773. The derivatives of the present invention have the 23-hydroxy group react to form a double bond in the 22,23 position. The novel derivatives of the present invention possess activity as anthelmintic, ectoparasitic, insecticidal, acaricidal and nematicidal agents. They also are useful in areas of human and animal health and in agricultural crops.

What is claimed is: 
     
       1. A compound represented by structural formula (I), ##STR7## wherein R 1  is methyl, ethyl or isopropyl; R 2  is hydrogen or methyl; R 3  is hydrogen, methyl or ethyl; R 4  is methyl or ethyl; or a pharmaceutically and pharmacologically acceptable salt thereof. 
     
     
       2. A compound according to claim 1, wherein R 1  is isopropyl; R 2  is hydrogen or methyl; R 3  is methyl; and R 4  is methyl. 
     
     
       3. A compound according to claim 2, wherein R 1  is isopropyl; R 2  is hydrogen; R 3  is methyl; and R 4  is methyl. 
     
     
       4. A method for the prevention, treatment or control of parasitic infections in warm-blooded animals, said method comprising: orally, topically or parenterally administering to an animal infected with parasites, a parasiticidally-effective amount of a compound represented by structural formula (I) ##STR8## wherein R 1  is methyl, ethyl or isopropyl; R 2  is hydrogen or methyl; R 3  is hydrogen, methyl or ethyl; R 4  is methyl or ethyl; or a pharmaceutically and pharmacologically acceptable salt thereof. 
     
     
       5. A method according to claim 4, wherein said compound has R 1  as isopropyl; R 2  is hydrogen or methyl; R 3  is methyl; and R 4  is methyl. 
     
     
       6. A method according to claim 5, wherein said compound has R 1  as isopropyl; R 2  is hydrogen; R 3  is methyl; and R 4  is methyl. 
     
     
       7. A method for protecting crops, trees, shrubs, stored grain and ornamentals from attack by insects and acarids which infect them, said method comprising: applying an acaricidally or insecticidally-effective amount of a compound represented by structural formula (I), ##STR9## wherein R 1  is methyl, ethyl or isopropyl; R 2  is hydrogen or methyl; R 3  is hydrogen, methyl or ethyl; R 4  is methyl or ethyl; or a pharmaceutically and pharmacologically acceptable salt thereof. 
     
     
       8. A method according to claim 7, wherein said compound is applied to the foliage of crops and plants, the soil in which they are grown or the trunk thereof. 
     
     
       9. A method according to claim 8, wherein said compound has R 1  as isopropyl; R 2  is hydrogen or methyl; R 3  is methyl; and R 4  is methyl. 
     
     
       10. A method according to claim 9, wherein said compound has R 1  as isopropyl; R 2  is hydrogen; R 3  is methyl; and R 4  is methyl. 
     
     
       11. A method for the control of plant nematodes, said method comprising: applying to the foliage of plants, the soil in which they are grown or into the trunks thereof, a nematocidally-effective amount of a compound represented by structural formula (I), ##STR10## wherein R 1  is methyl, ethyl or isopropyl; R 2  is hydrogen or methyl; R 3  is hydrogen, methyl or ethyl; R 4  is methyl or ethyl; or a pharmaceutically and pharmacologically acceptable salt thereof. 
     
     
       12. A method according to claim 11, wherein said compound has R 1  as isopropyl; R 2  is hydrogen or methyl; R 3  is methyl; and R 4  is methyl. 
     
     
       13. A method according to claim 12, wherein said compound has R 1  as isopropyl; R 2  is hydrogen; R 3  is methyl; and R 4  is methyl. 
     
     
       14. A composition comprising: a pharmacologically, acaricidally or insecticidally effective amount of a compound represented by structural formula (I), ##STR11## wherein R 1  is methyl, ethyl or isopropyl; R 2  is hydrogen or methyl; R 3  is hydrogen, methyl or ethyl; R 4  is methyl or ethyl; or a pharmaceutically and pharmacologically acceptable salt thereof: and an inert carrier; wherein said composition is used to control endo- or ectoparasitic pests which infect warm-blooded animals or to control acarid or insect pests which infest agricultural crops.